I have a feeling this will be going the route of online casinos. I'm also betting Apple is going to pull the plug on them.... or SF might be making some quick cash from Apple. I would be more impressed if the CEO actually is not operating in this manner, and actually ends up having his assets taken.

He's also not living anywhere near California. The startup is actually located in Rome, Italy. So, hopefully at some point this guy realizes that he's encouraging people to do exactly what the "distracted driving" laws are in place to prevent. The app requires you touch the screen to make certain actions, including:

• Request a parking spot• Bid on the spot• Call the other driver if you win the spot• Change your mind• Notify that you parked

You're allowed to check a map on a smartphone while driving, but you're not supposed to be overly engaged with it - or playing with your phone. (That's ticketable.) To make any call, it's supposed to be a fully hands-free action. So, just having a person "push the button" to call the other driver is an illegal form of cell phone use while driving.

If this MonkeyParking asshat is looking to go to the Supreme Court with this, I think he'll find that it will be a very expensive trip, and he'll lose long before he gets there.

As for the "holding a place in line" question, the line may be on a public sidewalk, but the "place" is not a public resource. The city of San Francisco doesn't have an interest in the line to buy an iPad. Now if someone were, say, renting plots of lawn in a public park where there was a concert, that would be illegal too. And rightfully so.

I'm rather perplexed about how many of these startups can function in America. Here as soon as you have someone offering a service in exchange for cash through a formal system (i.e. built so that you the entrepreneur can to take your % of the cut) you have the taxman right down on your ass because you're not paying into social security/health insurance/etc.You can barely get away with opening a Paypal account just to sell things on Ebay.

An app like MonkeyParking is only useful to the extent that unoccupied parking spaces are scarce, and they are only scarce if the city isn't charging enough for them. Some people might see empty parking spaces as waste- but they are not. What good are parking spaces if they are all occupied?Sure, if the city jacks up their rates the parking spaces will be occupied mainly by rich assholes, but it's not like that's a big change from the way things are now. They can use the extra revenue to build more parking ramps, or god forbid- better public transit.

If MonkeyParking was modified to report all payments to the city, and require the space holders to pay the city a 20% rake-off of all monies received, I feel safe in predicting that the lawsuit would evaporate by noon that same day.

As someone else pointed out somewhere, even if the app can legally exist, the city of SF can easily kill it. They can have SF police officers bid on spaces, bid enough to win, and when the driver pulls out a cop pulls the driver over and gives him/her a $300 ticket for illegally selling a parking space (that's what the law on the books says that the fine is). Even if MonkeyParking gets some of the money it will be less than $300, so the city makes a profit on every space they "buy". They can keep doing this until the word gets out, and maybe get the board of supervisors to raise the fine to $1000 just to rub it in.

I share your sentiment, but it's worth remembering that money isn't the only way to solve scarcity problems. Other solutions, including market-based solutions that don't involve money, can (and should) be explored. Making cars and parking something that only the rich can afford has all sorts of detrimental effects on urban areas, and public transit is not the solution for all of those problems.

No, they are selling the space, not information about the space. Information about the space might look like "this space will become available at 2PM". This would mean that anyone showing up at that time could snag the space. But that's not how it works. The seller squats on the space and holds it until he/she gets the notification that the buyer has arrived. This is done to make sure that the buyer gets the space, not just information about the space. So sorry, but this is a bogus attempt at a legal hack, and this kind of sophistry isn't going to get you out of the $300 fine.

Yes, and rightfully so. Parking space it's a public resource paid by the taxpayer to be accessible by all citizens. One of the means to ensure that they are used in moderation are parking meters – if they were free or could be used on a 24/7 basis, they would get hogged by a limited numbers of early birders.

Note how the shops who regularly moan that there isn't enough parking space for their customers are entirely free to provide them, well, for free. However, for some weird reason, they keep putting up signs with “Customer parking only”.